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Identification
- Summary
Arformoterol is a beta-2 adrenergic agonist and bronchodilator used for long-term, symptomatic treatment of reversible bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema.
- Brand Names
- Brovana
- Generic Name
- Arformoterol
- DrugBank Accession Number
- DB01274
- Background
Arformoterol is a bronchodilator. It works by relaxing muscles in the airways to improve breathing. Arformoterol inhalation is used to prevent bronchoconstriction in people with chronic obstructive pulmonary disease, including chronic bronchitis and emphysema. The use of arformoterol is pending revision due to safety concerns in regards to an increased risk of severe exacerbation of asthma symptoms, leading to hospitalization as well as death in some patients using long-acting beta agonists for the treatment of asthma.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Arformoterol (DB01274)
- Weight
- Average: 344.4049
Monoisotopic: 344.173607266 - Chemical Formula
- C19H24N2O4
- Synonyms
- (-)-formoterol
- (R,R)-formoterol
- Arformoterol
Pharmacology
- Indication
Arformoterol is indicated in the maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema.8
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Asthma Combination Product in combination with: Budesonide (DB01222) •••••••••••• •••••• Treatment of Bronchoconstriction •••••••••••• •••••••• Used in combination to manage Chronic obstructive pulmonary disease (copd) Combination Product in combination with: Budesonide (DB01222) •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Arformoterol, the active (R,R)-enantiomer of formoterol, is a selective long-acting β2-adrenergic receptor agonist (beta2-agonist) that has two-fold greater potency than racemic formoterol (which contains both the (S,S) and (R,R)-enantiomers). The (S,S)-enantiomer is about 1,000-fold less potent as a β2-agonist than the (R,R)-enantiomer. Arformoterol seems to have little or no effect on β1-adrenergic receptors.
- Mechanism of action
While it is recognized that β2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and β1-receptors are the predominant receptors in the heart, data indicate that there are also β2-receptors in the human heart comprising 10% to 50% of the total beta-adrenergic receptors. The precise function of these receptors has not been established, but they raise the possibility that even highly selective β2-agonists may have cardiac effects. The pharmacologic effects of β2-adrenoceptor agonist drugs, including arformoterol, are at least in part attributable to the stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3,5-adenosine monophosphate (cyclic AMP). Increased intracellular cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of the release of proinflammatory mediators from cells, especially from mast cells. In vitro tests show that arformoterol is an inhibitor of the release of mast cell mediators, such as histamine and leukotrienes, from the human lung. Arformoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-response.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - Absorption
In patients with COPD, the mean peak plasma concentration (Cmax) and AUC0-12h following twice daily administration for 14 days were 4.3 pg/mL and 34.5 pg.hr/mL, respectively.8 The time to peak plasma concentration (Tmax) was approximately 0.5 hours.8
- Volume of distribution
Not Available
- Protein binding
The binding of arformoterol to human plasma proteins in vitro was 52-65% at concentrations of 0.25, 0.5 and 1.0 ng/mL of radiolabeled arformoterol.
- Metabolism
Arformoterol was almost entirely metabolized following oral administration of 35 mcg of radiolabeled arformoterol in eight healthy subjects. Direct conjugation of arformoterol with glucuronic acid was the major metabolic pathway. O-Desmethylation is a secondary route catalyzed by the CYP enzymes CYP2D6 and CYP2C19.
- Route of elimination
Following the administration of a single oral dose of arformoterol to eight healthy subjects, 63% of the administered dose was recovered in the urine and 11% in the feces within 48 hours.8 After 14 days, a total of 89% of the total dose had been recovered - 67% in the urine and 22% in the feces - with approximately 1% remaining unchanged in the urine.8
- Half-life
In COPD patients given 15 mcg inhaled arformoterol twice a day for 14 days, the mean terminal half-life of arformoterol was 26 hours.8
- Clearance
In healthy male subjects, the clearance of a single oral dose of arformoterol was 8.9 L/h.8
- Adverse Effects
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A death was reported in dogs after a single oral dose of 5 mg/kg (approximately 4500 times the maximum recommended daily inhalation dose in adults on a mg/m2 basis). As with all inhaled sympathomimetic medications, cardiac arrest and even death may be associated with an overdose. Arformoterol should not be used more often or at higher doses than recommended, or conjunction with other medications containing long-acting beta2-agonists.8
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Arformoterol which could result in a higher serum level. Abatacept The metabolism of Arformoterol can be increased when combined with Abatacept. Abiraterone The metabolism of Arformoterol can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Arformoterol. Acebutolol The therapeutic efficacy of Arformoterol can be decreased when used in combination with Acebutolol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Arformoterol tartrate 5P8VJ2I235 200815-49-2 FCSXYHUNDAXDRH-OKMNHOJOSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Brovana Solution 15 ug/2mL Respiratory (inhalation) Sumitomo Pharma America, Inc. 2007-04-01 2024-01-01 US 
Brovana Solution 15 ug/2mL Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2024-04-15 Not applicable US Brovana Solution 15 ug/2mL Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2023-10-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Arformoterol Tartrate Solution 15 ug/2mL Respiratory (inhalation) Dr. Reddy's Laboratories Limited 2024-09-02 Not applicable US Arformoterol tartrate Solution 15 ug/2mL Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2022-07-27 Not applicable US Arformoterol Tartrate Solution 15 ug/2mL Respiratory (inhalation) Northstar RxLLC 2024-06-01 Not applicable US Arformoterol Tartrate Solution 15 ug/2mL Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2021-06-01 2023-11-30 US Arformoterol Tartrate Solution 15 ug/2mL Respiratory (inhalation) Lifestar Pharma Llc 2022-11-15 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AIRBIR 3/100 MCG INHALASYON IÇIN TOZ IÇEREN KAPSÜL, 120 KPS Arformoterol (3 mcg) + Budesonide (100 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
AIRBIR 3/100 MCG INHALASYON IÇIN TOZ IÇEREN KAPSÜL, 60 KPS Arformoterol (3 mcg) + Budesonide (100 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey AIRBIR 3/200 MCG INHALASYON IÇIN TOZ IÇEREN KAPSÜL ,120 KAPSÜL Arformoterol (3 mcg) + Budesonide (200 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey AIRBIR 3/200 MCG INHALASYON IÇIN TOZ IÇEREN KAPSÜL ,60 KAPSÜL Arformoterol (3 mcg) + Budesonide (200 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey AIRBIR 6/200 MCG INHALASYON IÇIN TOZ IÇEREN KAPSÜL, 120 ADET Arformoterol (6 mcg) + Budesonide (200 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Autonomic Agents
- Bronchodilator Agents
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Ethanolamines
- Long-acting beta-adrenoceptor agonists
- Peripheral Nervous System Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Respiratory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Amphetamines and derivatives
- Alternative Parents
- Phenylpropanes / Anilides / Phenoxy compounds / N-arylamides / Methoxybenzenes / Anisoles / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Aralkylamines / Secondary carboxylic acid amides show 9 more
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Amphetamine or derivatives / Anilide / Anisole / Aralkylamine show 23 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- N-[2-hydroxy-5-(1-hydroxy-2-\{[1-(4-methoxyphenyl)propan-2-yl]amino\}ethyl)phenyl]formamide (CHEBI:408174)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- F91H02EBWT
- CAS number
- 67346-49-0
- InChI Key
- BPZSYCZIITTYBL-YJYMSZOUSA-N
- InChI
- InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
- IUPAC Name
- N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
- SMILES
- COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1
References
- Synthesis Reference
Vaman Vaishali Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan, "Process for the Synthesis of Arformoterol." U.S. Patent US20110166237, issued July 07, 2011.
US20110166237- General References
- Hanania NA, Donohue JF, Nelson H, Sciarappa K, Goodwin E, Baumgartner RA, Hanrahan JP: The safety and efficacy of arformoterol and formoterol in COPD. COPD. 2010 Feb;7(1):17-31. doi: 10.3109/15412550903499498. [Article]
- Donohue JF, Hanania NA, Sciarappa KA, Goodwin E, Grogan DR, Baumgartner RA, Hanrahan JP: Arformoterol and salmeterol in the treatment of chronic obstructive pulmonary disease: a one year evaluation of safety and tolerance. Ther Adv Respir Dis. 2008 Apr;2(2):37-48. doi: 10.1177/1753465808089455. [Article]
- Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [Article]
- Panettieri RA Jr, MacIntyre N, Sims M, Kerwin E, Fogarty C, Noonan M, Claus R, Andrews WT: Comparison of the efficacy and safety of arformoterol 15 microg twice daily and arformoterol 30 microg once daily in COPD: a single-dose, multicenter, randomized, modified-blind, two-way crossover study. Clin Ther. 2009 Aug;31(8):1716-23. doi: 10.1016/j.clinthera.2009.08.012. [Article]
- Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [Article]
- Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [Article]
- TITCK Product Information: Airbir (arformoterol tartrate/budesonide) capsule with powder for inhalation [Link]
- FDA Approved Drug Products: Brovana (arformoterol tartrate) solution for inhalation [Link]
- External Links
- Human Metabolome Database
- HMDB0015399
- KEGG Drug
- D07463
- PubChem Compound
- 3083544
- PubChem Substance
- 46506392
- ChemSpider
- 2340731
- BindingDB
- 50151720
- 304962
- ChEBI
- 408174
- ChEMBL
- CHEMBL1363
- ZINC
- ZINC000002599970
- Therapeutic Targets Database
- DAP000943
- PharmGKB
- PA164743977
- PDBe Ligand
- H98
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Arformoterol
- PDB Entries
- 6ibl / 6tko / 7bz2 / 8jj8
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Diagnostic Chronic Obstructive Pulmonary Disease (COPD) 1 somestatus stop reason just information to hide Not Available Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 somestatus stop reason just information to hide 4 Completed Treatment Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 3 somestatus stop reason just information to hide 4 Terminated Treatment Asthma Acute 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Cardinal Health
- Catalent Pharma Solutions
- Sepracor Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Powder Respiratory (inhalation) Solution Respiratory (inhalation) 15 ug/2mL Powder Respiratory (inhalation) - Prices
Unit description Cost Unit Brovana 15 mcg/2 ml solution 3.41USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5795564 No 1998-08-18 2012-04-03 US US6814953 No 2004-11-09 2021-06-22 US US7348362 No 2008-03-25 2021-06-22 US US7462645 No 2008-12-09 2021-06-22 US US7473710 No 2009-01-06 2021-06-22 US US7541385 No 2009-06-02 2021-06-22 US US6667344 No 2003-12-23 2021-06-22 US US6040344 No 2000-03-21 2016-11-12 US US8110706 No 2012-02-07 2021-11-09 US US7465756 No 2008-12-16 2021-06-22 US US6720453 No 2004-04-13 2021-11-09 US US6472563 No 2002-10-29 2021-11-09 US US7145036 No 2006-12-05 2021-11-09 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0416 mg/mL ALOGPS logP 1.91 ALOGPS logP 1.06 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 8.61 Chemaxon pKa (Strongest Basic) 9.81 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 90.82 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 97.87 m3·mol-1 Chemaxon Polarizability 36.56 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8991 Blood Brain Barrier - 0.8026 Caco-2 permeable - 0.6916 P-glycoprotein substrate Substrate 0.747 P-glycoprotein inhibitor I Non-inhibitor 0.8773 P-glycoprotein inhibitor II Non-inhibitor 0.8561 Renal organic cation transporter Non-inhibitor 0.8818 CYP450 2C9 substrate Non-substrate 0.714 CYP450 2D6 substrate Non-substrate 0.7086 CYP450 3A4 substrate Substrate 0.5556 CYP450 1A2 substrate Non-inhibitor 0.6609 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8757 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8442 Ames test Non AMES toxic 0.7517 Carcinogenicity Non-carcinogens 0.8704 Biodegradation Not ready biodegradable 0.992 Rat acute toxicity 2.4047 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9611 hERG inhibition (predictor II) Non-inhibitor 0.6602
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00or-2902000000-10d83ebb89a446028d15 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00kb-0339000000-4770ea45defc3ce5dd7d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00kf-0039000000-580612758f9fa39d013d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0axs-0595000000-98fa7f0601b82bf7bd69 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4m-2291000000-4d74be9d2942b9535015 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0293000000-9aa9d932000b1476cd8c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-1943000000-6ce745c4ba53a4187edb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.3089367 predictedDarkChem Lite v0.1.0 [M-H]- 190.1401367 predictedDarkChem Lite v0.1.0 [M-H]- 185.82632 predictedDeepCCS 1.0 (2019) [M+H]+ 200.5407367 predictedDarkChem Lite v0.1.0 [M+H]+ 189.7561367 predictedDarkChem Lite v0.1.0 [M+H]+ 188.18434 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.1983367 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.3707367 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.78798 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Authors unspecified: Arformoterol: (R,R)-eformoterol, (R,R)-formoterol, arformoterol tartrate, eformoterol-sepracor, formoterol-sepracor, R,R-eformoterol, R,R-formoterol. Drugs R D. 2004;5(1):25-7. [Article]
- Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [Article]
- Matera MG, Cazzola M: ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD? Drugs. 2007;67(4):503-15. [Article]
- Cazzola M, Hanania NA, Matera MG: Arformoterol tartrate in the treatment of COPD. Expert Rev Respir Med. 2010 Apr;4(2):155-62. doi: 10.1586/ers.10.16. [Article]
- Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [Article]
- Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [Article]
- Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [Article]
- Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [Article]
- Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [Article]
- Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [Article]
- Formoterol FDA Label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [Article]
- Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [Article]
- Formoterol FDA Label [File]
Drug created at May 16, 2007 20:28 / Updated at June 02, 2024 21:56